WO2014059061A1 - Use of perturbants to facilitate incorporation and recovery of taggants from polymerized coatings - Google Patents

Use of perturbants to facilitate incorporation and recovery of taggants from polymerized coatings Download PDF

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Publication number
WO2014059061A1
WO2014059061A1 PCT/US2013/064194 US2013064194W WO2014059061A1 WO 2014059061 A1 WO2014059061 A1 WO 2014059061A1 US 2013064194 W US2013064194 W US 2013064194W WO 2014059061 A1 WO2014059061 A1 WO 2014059061A1
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WO
WIPO (PCT)
Prior art keywords
taggant
perturbant
dna
polymer
solution
Prior art date
Application number
PCT/US2013/064194
Other languages
English (en)
French (fr)
Inventor
Lawrence JUNG
Benjamin Minghwa LIANG
James A. Hayward
Original Assignee
Applied Dna Sciences Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Applied Dna Sciences Inc. filed Critical Applied Dna Sciences Inc.
Priority to EP13845351.9A priority Critical patent/EP2906721B1/en
Priority to AU2013329256A priority patent/AU2013329256B2/en
Priority to CA2886472A priority patent/CA2886472C/en
Priority to JP2015536872A priority patent/JP2016500518A/ja
Publication of WO2014059061A1 publication Critical patent/WO2014059061A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
    • C12Q1/6806—Preparing nucleic acids for analysis, e.g. for polymerase chain reaction [PCR] assay
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids

Definitions

  • the present invention relates to methods for facilitating the inclusion of traceable taggants into polymers and for the recovery and detection of such taggants without altering the aesthetic appearance of the object or the matrix of the object.
  • nucleic acids are capable of encoding a vast array of information: witness the human genome encodes all the information necessary for the synthesis and assembly of all the components of the human body from the neural networks of the brain to the intricate structures of the skeleton, tissues and organs. Nucleic acids include
  • a method for facilitating the inclusion of traceable taggants into a polymer matrix useful for coating an object includes incorporating a taggant into a solution, mixing the solution including the taggant with a perturbant to form a first perturbant taggant solution, mixing the first perturbant taggant solution with a polymer to form a second perturbant taggant solution and applying the second perturbant taggant solution to at least a portion of the object to form a taggant-coated portion of the object.
  • a method for authenticating an object includes providing an object comprising a coating that includes a taggant such as a nucleic acid, a perturbant such as a polyol and a polymer coating; recovering the taggant from the object and verifying the authenticity of the object by identifying the taggant.
  • a taggant such as a nucleic acid
  • a perturbant such as a polyol
  • a polymer coating includes recovering the taggant from the object and verifying the authenticity of the object by identifying the taggant.
  • PCR includes but is not limited to standard PCR methods, where in DNA strands are copied to provide a million or more copies of the original DNA strands (e.g. PCR using random primers: See for instance PCR with Arbitrary Primers: Approach with Care. W.C. Black IV, Ins. Mol. Biol. 2: 1-6, Dec.
  • the term "monomer” as used herein refers to any chemical entity that can be covalently linked to one or more other such entities to form an oligomer or a polymer.
  • Examples of “monomers” include nucleotides, amino acids, saccharides, amino acids, and the like.
  • nucleic acid means a polymer composed of nucleotides which can be deoxyribonucleotides or ribonucleotides. These compounds can be natural or synthetically produced deoxyribonucleotides or ribonucleotides.
  • the synthetically produced nucleic acid can be of a naturally occurring sequence, or a non-natural unique sequence.
  • oligonucleotide refers to single or double stranded polymer composed of covalently nucleotide monomers forming a chain of from two to about twenty nucleotides in length.
  • polynucleotide refers to single or double stranded polymer composed of covalently nucleotide monomers forming a chain of generally greater than about twenty nucleotides in length.
  • Nucleic acids having a naturally occurring sequence can hybridize with nucleic acids in a sequence specific manner. That is they can participate in hybridization reactions in which the complementary base pairs A:T (adenine:thymine) and G:C (guanine:cytosine) form intermolecular (or intra-molecular) hydrogen bonds and cooperative stacking interactions between the planar neighboring bases in each strand through Pi electrons, together known as Watson-Crick base pairing interactions.
  • A:T adenine:thymine
  • G:C guanine:cytosine
  • the bases of the nucleic acid strands can also hybridize to form non-Watson-Crick base pairs by so-called "wobble" interactions in which G (guanine) pairs with U (uracil), or alternatively, I (inosine) pairs with C (cytosine), U (uracil) or A (adenine).
  • Exemplary embodiments provide methods for increasing the recoverability of a taggant from an object without disturbing the appearance of the object.
  • Several exemplary embodiments of the present invention are described in detail below.
  • an exemplary embodiment of the invention provides a method for increasing the recoverability of a taggant from an object; the method includes incorporating a taggant into a solvent, mixing the solution including the taggant with a perturbant to form a first perturbant taggant solution, mixing the first perturbant taggant solution with a polymer to form a second taggant solution and applying the second taggant solution to at least a portion of the object to form a taggant-coated portion of the object.
  • the taggant can be soluble in an aqueous solution.
  • an aqueous soluble taggant examples include nucleic acids, saccharides, peptides and many proteins.
  • the taggant can be insoluble in an aqueous solution, or an organic solvent.
  • a taggant that is insoluble in aqueous solutions or organic solvents include particulate taggants, such as for instance, a up-converting phosphor (UCP) taggant, which may be any suitable UCP taggant, such as a nucleic acid-linked UCP.
  • UCP up-converting phosphor
  • nylon 6, nylon 66 polypropylene (PP), polyvinyl chloride (PVC), polysulphones, polyvinylacetate (PVA), polyester (PES), polyethylene terephthalate (PET), polyethylene (PE), benzocyclobutene (BCB), high- density polyethylene (HDPE), polyvinylidene chloride (PVDC), low-density
  • polymers into which a taggant can be incorporated according to the methods of the present invention and which can also be used for coating all or part of the surface of an object include, for example, acrylic compounds such as polymethyl methacrylate (PMMA), a transparent thermoplastic synthetic polymer of methyl methacrylate, also called acrylic glass; and acrylic copolymers such as polymethyl methacrylate -polyacrylonitrile copolymers; and the thermosetting epoxy-based polymer compounds such as epoxy-copolymers formed by polymerization of a resin compound and a hardener or activator.
  • the resin is a monomer or short chain having an epoxy group at each terminus.
  • the epoxy-based compound that includes the taggant of the present invention can include compounds and resins having two or more epoxy groups. These compounds may be in liquid, gel-like or in solid form.
  • epoxy-based compounds useful in the practice of the present invention include epoxy resins such as: glycidyl ethers obtained by reacting epichlorohydrin with a polyhydric phenol such as bisphenol A, bisphenol F, bisphenol S, hexahydrobisphenol A, tetramethylbisphenol A, diallyl-bisphenol A, hydroquinone, catechol, resorcin, cresol, tetrabromobisphenol A, trihydroxybiphenyl, benzophenone, bisresorcinol, bisphenol hexafluoroacetone, tetramethylbisphenol A, tetramethylbisphenol F,
  • the polymer is for example, a natural polymer, a varnish, a polyurethane, a shellac or a lacquer.
  • the varnish, polyurethane, shellac or lacquer can be any suitable varnish, polyurethane, shellac or lacquer, such as for instance and without limitation, a polyurethane varnish from Minwax ® Co., Upper Saddle River, NJ.
  • the polymer useful as a coating can be a natural polymer, such as beeswax, e.g. the beeswax available from Mountain Rose Herbs, Eugene, OR.
  • the polymer is a component of a polymer-containing composition, such as for example, a printing ink.
  • the ink may be a heat-curing epoxy-acrylate ink, such as Product No. 4408R or the 970 series Touch Dry ® pellet each from Markem ® , Keene, NH.
  • the Artistri ® P5000 + Series-Pigment Ink sold by Dupont ® ' or an Epoxy Acrylate Ink, such as Product No. 00-988, Rahn USA Corp. can be used.
  • the taggants of the present invention include, for example, nucleic acid taggants.
  • Nucleic acid is a general term for deoxyribonucleic acid (DNA) or ribonucleic acid (RNA), and can be synthetic, or derived from an animal, a plant, a bacterium, a virus, a fungus, or a synthetic vector or a fragment of any of the above-listed nucleic acids, etc.
  • a synthetic nucleic acid can have a sequence of a naturally occurring nucleic acid of an animal, plant, bacterium, fungus, virus or any other organism or synthetic vector.
  • a synthetic nucleic acid can have a unique sequence not found in nature.
  • the perturbant of the present invention can be used in a solution containing the polymer and the taggant in an amount of about 7 % to about 15% w/w of the taggant in the solution. In still another exemplary embodiment, the perturbant of the present invention can be used in a solution containing the polymer and the taggant in an amount of about % 10 w/w of the taggant in the solution.
  • the coating that includes or incorporates a taggant of the invention which can be applied to an object of interest can be any suitable coating which is stable and capable of incorporating the taggant, for example, a plastic, a varnish, a
  • the polymer is a varnish, a polyurethane, a shellac or a lacquer.
  • the solution enhancer includes at least one polyol.
  • the polyol can be any suitable polyol, such as for ethylene glycol, diethylene glycol, glycerol, methanediol, 1,2-butanediol, 1,4-butanediol, triethylene glycol, propylene glycol, and polyethylene glycol (PEG).
  • the polyethylene glycol can be of any suitable size, such as for instance and without limitation, PEG 200, PEG 400, PEG 600, PEG 2000, PEG 3350 or PEG 10,000.
  • DNA taggants useful in the examples described below include any suitable DNA taggant, such as for instance, in one embodiment, the DNA taggant is a double stranded DNA oligomer having a length of between about 40 base pairs and about 1000 base pairs. In other embodiments the DNA taggant is a double stranded DNA oligomer with a length of between about 80 and 500 base pairs. In another embodiment the DNA taggant is a double stranded DNA oligomer having a length of between about 100 and about 250 base pairs. Alternatively, the DNA taggant can be single-stranded DNA or any suitable length, such as between about 40 bases and about 1000 bases;
  • the DNA taggant is identifiable by any suitable detection and/or identification method such as for example, hybridization with a taggant-sequence specific nucleic acid probe, an in situ hybridization method (including fluorescence in situ hybridization: FISH), amplification using a polymerase chain reaction (PCR), such as quantitative/real time PCR and detection of the amplified sequences (amplicons) by any of the variety of standard well known methods.
  • a suitable detection and/or identification method such as for example, hybridization with a taggant-sequence specific nucleic acid probe, an in situ hybridization method (including fluorescence in situ hybridization: FISH), amplification using a polymerase chain reaction (PCR), such as quantitative/real time PCR and detection of the amplified sequences (amplicons) by any of the variety of standard well known methods.
  • FISH fluorescence in situ hybridization
  • PCR polymerase chain reaction
  • the sample recovered from the examined object does not include the unique nucleic acid corresponding to the authentic object, there will likely be no amplified nucleic acid product, or if the primers do amplify the recovered nucleic acid to produce one or more random amplicons, these one or more amplicons cannot have the unique taggant nucleic acid sequence from the authentic object.
  • the random amplicons derived from counterfeit articles are also of random lengths and the likelihood of producing amplicons of the exact lengths specified by the taggant-specific primers is vanishingly small. Therefore, by comparing the sizes of PCR products, the authenticity of labeled objects can be verified, non-authentic objects can be screened and rejected and anti-counterfeit screening purpose is then achieved.
  • UCP IR taggant e.g. ADA-3253 from H.W.
  • DNA taggant 10 ng/ml of DNA taggant (final concentration) is added to 100 ppm of molten PEG3350 average M n 3000-3700, Product No. 83272, Sigma- Aldrich) before being added to 1L of molten beeswax (Mountainroseherbs.com, Eugene, OR)
  • the DNA is purified from the wax and the DNA is then authenticated by utilizing a PCR based assay
  • DNA taggant 10 ng/ml of DNA taggant (final concentration) is added to 1% of PEG200 average M n 200, Product No. P3015, Sigma-Aldrich) before being mixed into 1L of a solvent based inkjet ink (such as the 970 series Touch Dry ® pellet; or the 4408R heat- curing ink sold by Markem ® , Keene, NH; the Artistri ® P5000 + Series-Pigment Ink sold by Dupont ® , or the Epoxy Acrylate Ink, Product No. 00-988, Rahn USA Corp.).
  • a solvent based inkjet ink such as the 970 series Touch Dry ® pellet; or the 4408R heat- curing ink sold by Markem ® , Keene, NH; the Artistri ® P5000 + Series-Pigment Ink sold by Dupont ® , or the Epoxy Acrylate Ink, Product No. 00-988, Rahn USA Corp

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Molecular Biology (AREA)
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  • Biotechnology (AREA)
  • Biophysics (AREA)
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  • Genetics & Genomics (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
  • Luminescent Compositions (AREA)
PCT/US2013/064194 2012-10-10 2013-10-10 Use of perturbants to facilitate incorporation and recovery of taggants from polymerized coatings WO2014059061A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP13845351.9A EP2906721B1 (en) 2012-10-10 2013-10-10 Use of perturbants to facilitate incorporation and recovery of nucleic acid taggants from polymerized coatings
AU2013329256A AU2013329256B2 (en) 2012-10-10 2013-10-10 Use of perturbants to facilitate incorporation and recovery of taggants from polymerized coatings
CA2886472A CA2886472C (en) 2012-10-10 2013-10-10 Use of perturbants to facilitate incorporation and recovery of taggants from polymerized coatings
JP2015536872A JP2016500518A (ja) 2012-10-10 2013-10-10 重合コーティングにおけるタガントの組み込みおよび回収を容易にするための摂動剤の使用

Applications Claiming Priority (2)

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US13/648,594 US9297032B2 (en) 2012-10-10 2012-10-10 Use of perturbants to facilitate incorporation and recovery of taggants from polymerized coatings
US13/648,594 2012-10-10

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WO2014059061A1 true WO2014059061A1 (en) 2014-04-17

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US (2) US9297032B2 (enrdf_load_stackoverflow)
EP (1) EP2906721B1 (enrdf_load_stackoverflow)
JP (1) JP2016500518A (enrdf_load_stackoverflow)
AU (1) AU2013329256B2 (enrdf_load_stackoverflow)
CA (1) CA2886472C (enrdf_load_stackoverflow)
WO (1) WO2014059061A1 (enrdf_load_stackoverflow)

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US9297032B2 (en) 2016-03-29
CA2886472A1 (en) 2014-04-17
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EP2906721B1 (en) 2018-12-05
US10059981B2 (en) 2018-08-28
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